William Shakespeare's birthplace in Stratford-Upon-Avon (Photograph by eye35.pix, Alamy)

Like many of you out there, I slogged my way through Shakespeare in English Lit classes (that Shakespeare intended his work to be performed rather than read may offer some explanation), but certain melodious fragments–“All’s well that ends well” and “We know what we are, but know not what we may be” among them–continue to enthrall me.

The Bard of Avon was born 450 years ago and, rightly so, England is celebrating his enduring legacy. Rather than zipping over to Stratford for the day and checking off Shakespeare sites from a list, I wanted to experience the landscapes that inspired his words. That’s how I found myself ordering waterproof shoes, packing light layers and Lycra, and landing in London to bike Shakespeare’s Way, a self-guided route developed by the family-owned Carter Company.

Blenheim Palace, family property of the Dukes of Marlborough, was built in 1722. (Photograph by Annie Fitzsimmons)

Biking as sightseeing mechanism has risen in popularity worldwide in recent years, and England is embracing the trend. Just last year, the government announced that it would be devoting £94 million to improve its cycling infrastructure.

Wendy Carter, a charming dame who has built up a remarkable familiarity with England’s bicycle trails over a period of 25 years, assured me that this wasn’t going to be an intense Tour-de-France-style trip. Instead, her company promotes “gentle cycling,” a slower approach that allows riders to really drink in their surroundings. It sounded like the perfect fit for me, a casual yet devoted cyclist who can handle up to 40 relatively flat miles a day with the occasional arduous hill thrown in.

Shakespeare’s Way picks up in Stratford and, though I enjoyed stopovers at classic sites (his birthplace and grave, his wife Anne Hathaway’s childhood home), I felt closest to his essence while pedaling through the English countryside, with its thatched roofs, fragrant gardens, and stone walls. I felt I was as close as I could ever come to hugging a country.

The route is clearly the result of hard-won local intelligence. I biked through neighborhoods as kids walked home from school, nabbed a lovely view of the Long Walk to Windsor Castle, and rode the length of Dorney Lake, where Eton College boys row, through a mist and past the entrance to the famous boarding school (Princes William and Harry are two of countless famous grads).

A bike path along the Thames River (Photograph by Annie Fitzsimmons)

After indulging my love for grassy quads with a night in Oxford and witnessing students in fleece–the nation’s next generation of leaders no doubt–downing pints at the Turf Tavern, I pedaled through a panorama of countryside en route to the majestic Blenheim Palace.

I love a mix of higher-end and casual dining, on any trip, and this itinerary delivered. A mid-day stop at Daylesford Organic Farm–a leader in England’s sustainable farming movement for decades–was especially memorable, as was the Hind’s Head in Bray-on-Thames. The latter, owned by avant-garde chef Heston Blumenthal, feels like a well-loved country pub where the food’s been kicked up a notch (don’t miss the tea-smoked salmon or bubble and squeak with a perfectly poached egg).

Biking into London along the Thames provided an insider’s welcome to the capital I never would have gotten from inside a car. And, of course, no Shakespeare tour is complete without a visit to Shakespeare’s Globe, a reproduction of the historic theater built by the bard’s playing company, to bring my tour full circle.

Looking back on my trip, my most memorable and energizing moments were spent cruising through the tiny towns in the Cotswolds and the beech woods of the Chilterns, two distinctive yet equally beautiful landscapes. As I climbed a particularly grueling hill and whizzed down the other side, red-cheeked and gulping cold air, it occurred to me that this corner of the English countryside has managed to remain largely unchanged in an ever-changing world.

That’s just what Shakespeare–and his wonderful ear for language–offers us. He once wrote, “Things won are done; joy’s soul lies in the doing.” I may never win the Tour de France, but the joy of bike riding as a vehicle for discovery will never grow old.

Annie Fitzsimmons is Intelligent Travel’s Urban Insider, giving you the dish on the best things to see and do in cities all over the world. Follow her on Twitter @anniefitz and on Instagram @anniefitzsimmons.